diff --git a/.gitignore b/.gitignore
index 70bef39d..379afe40 100644
--- a/.gitignore
+++ b/.gitignore
@@ -37,6 +37,7 @@ config/settings.json
 
 # logs
 config/logs/*.log*
+config/logs/*.json
 
 # dist files
 dist
diff --git a/package.json b/package.json
index ac024cec..ac3414c1 100644
--- a/package.json
+++ b/package.json
@@ -53,6 +53,7 @@
     "typeorm": "^0.2.29",
     "uuid": "^8.3.2",
     "winston": "^3.3.3",
+    "winston-daily-rotate-file": "^4.5.0",
     "xml2js": "^0.4.23",
     "yamljs": "^0.3.0",
     "yup": "^0.32.8"
diff --git a/server/logger.ts b/server/logger.ts
index 06c7d025..75e80151 100644
--- a/server/logger.ts
+++ b/server/logger.ts
@@ -1,5 +1,17 @@
 import * as winston from 'winston';
+import 'winston-daily-rotate-file';
 import path from 'path';
+import fs from 'fs';
+
+// Migrate away from old log
+const OLD_LOG_FILE = path.join(__dirname, '../config/logs/overseerr.log');
+if (fs.existsSync(OLD_LOG_FILE)) {
+  const file = fs.lstatSync(OLD_LOG_FILE);
+
+  if (!file.isSymbolicLink()) {
+    fs.unlinkSync(OLD_LOG_FILE);
+  }
+}
 
 const hformat = winston.format.printf(
   ({ level, label, message, timestamp, ...metadata }) => {
@@ -29,10 +41,14 @@ const logger = winston.createLogger({
         hformat
       ),
     }),
-    new winston.transports.File({
-      filename: path.join(__dirname, '../config/logs/overseerr.log'),
-      maxsize: 20971520,
-      maxFiles: 6,
+    new winston.transports.DailyRotateFile({
+      filename: path.join(__dirname, '../config/logs/overseerr-%DATE%.log'),
+      datePattern: 'YYYY-MM-DD',
+      zippedArchive: true,
+      maxSize: '20m',
+      maxFiles: '7d',
+      createSymlink: true,
+      symlinkName: 'overseerr.log',
     }),
   ],
 });
diff --git a/yarn.lock b/yarn.lock
index 47865d02..a941d705 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6114,6 +6114,13 @@ file-entry-cache@^6.0.0:
   dependencies:
     flat-cache "^3.0.4"
 
+file-stream-rotator@^0.5.7:
+  version "0.5.7"
+  resolved "https://registry.yarnpkg.com/file-stream-rotator/-/file-stream-rotator-0.5.7.tgz#868a2e5966f7640a17dd86eda0e4467c089f6286"
+  integrity sha512-VYb3HZ/GiAGUCrfeakO8Mp54YGswNUHvL7P09WQcXAJNSj3iQ5QraYSp3cIn1MUyw6uzfgN/EFOarCNa4JvUHQ==
+  dependencies:
+    moment "^2.11.2"
+
 file-uri-to-path@1.0.0:
   version "1.0.0"
   resolved "https://registry.yarnpkg.com/file-uri-to-path/-/file-uri-to-path-1.0.0.tgz#553a7b8446ff6f684359c445f1e37a05dacc33dd"
@@ -9050,7 +9057,7 @@ moment-timezone@^0.5.31:
   dependencies:
     moment ">= 2.9.0"
 
-"moment@>= 2.9.0":
+"moment@>= 2.9.0", moment@^2.11.2:
   version "2.29.1"
   resolved "https://registry.yarnpkg.com/moment/-/moment-2.29.1.tgz#b2be769fa31940be9eeea6469c075e35006fa3d3"
   integrity sha512-kHmoybcPV8Sqy59DwNDY3Jefr64lK/by/da0ViFcuA4DH0vQg5Q6Ze5VimxkfQNSC+Mls/Kx53s7TjP1RhFEDQ==
@@ -9828,7 +9835,7 @@ object-copy@^0.1.0:
     define-property "^0.2.5"
     kind-of "^3.0.3"
 
-object-hash@^2.0.3:
+object-hash@^2.0.1, object-hash@^2.0.3:
   version "2.0.3"
   resolved "https://registry.yarnpkg.com/object-hash/-/object-hash-2.0.3.tgz#d12db044e03cd2ca3d77c0570d87225b02e1e6ea"
   integrity sha512-JPKn0GMu+Fa3zt3Bmr66JhokJU5BaNBIh4ZeTlaCBzrBsOeXzwcKKAK1tbLiPKgvwmPXsDvvLHoWh5Bm7ofIYg==
@@ -14157,7 +14164,17 @@ widest-line@^3.1.0:
   dependencies:
     string-width "^4.0.0"
 
-winston-transport@^4.4.0:
+winston-daily-rotate-file@^4.5.0:
+  version "4.5.0"
+  resolved "https://registry.yarnpkg.com/winston-daily-rotate-file/-/winston-daily-rotate-file-4.5.0.tgz#3914ac57c4bdae1138170bec85af0c2217b253b1"
+  integrity sha512-/HqeWiU48dzGqcrABRlxYWVMdL6l3uKCtFSJyrqK+E2rLnSFNsgYpvwx15EgTitBLNzH69lQd/+z2ASryV2aqw==
+  dependencies:
+    file-stream-rotator "^0.5.7"
+    object-hash "^2.0.1"
+    triple-beam "^1.3.0"
+    winston-transport "^4.2.0"
+
+winston-transport@^4.2.0, winston-transport@^4.4.0:
   version "4.4.0"
   resolved "https://registry.yarnpkg.com/winston-transport/-/winston-transport-4.4.0.tgz#17af518daa690d5b2ecccaa7acf7b20ca7925e59"
   integrity sha512-Lc7/p3GtqtqPBYYtS6KCN3c77/2QCev51DvcJKbkFPQNoj1sinkGwLGFDxkXY9J6p9+EPnYs+D90uwbnaiURTw==